Trifluoroacetic acid → 4-(6-Bromo-10H-9-oxa-3-thiabenzo[f]azulen-4-ylidene)-1-methylpiperidine

6-Bromo-10H-9-oxa-3-thiabenzo[f]azulen-4-one (21.6 g, 100 mmol) was added to a Grignard reagent prepared from 4-chloro-N-methylpiperidine (20 mL, 150 mmol), a metal magnesium (3.6 g, 150 mmol), dibromoethane (0.1 mL), and THF (200 mL). The reaction mixture was stirred at room temperature for 2 hours, a saturated aqueous ammonium chloride solution was added to the solution to stop the reaction, and a product was then extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvents were distilled off under a reduced pressure, the resulting residue was dissolved in dichloromethane (300 mL), trifluoroacetic acid (77 mL, 1.0 mol) was added thereto, and the mixture was stirred overnight. The solvents were distilled off under a reduced pressure, and a saturated aqueous sodium bicarbonate solution was added to the residue. The product was extracted with ethyl acetate, and the extract was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvents were distilled off under a reduced pressure, and the resulting residue was then purified by column chromatography (hexane-ethyl acetate=3:2), to give 16.2 g (81%) of the captioned compound.

1. customthe reaction
2. extractiona product was then extracted with ethyl acetate
3. washThe organic layer was washed with a saturated sodium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. distillationThe solvents were distilled off under a reduced pressure
6. dissolutionthe resulting residue was dissolved in dichloromethane (300 mL)
7. stirringthe mixture was stirred overnight
8. distillationThe solvents were distilled off under a reduced pressure
9. additiona saturated aqueous sodium bicarbonate solution was added to the residue
10. extractionThe product was extracted with ethyl acetate
11. washthe extract was washed with a saturated sodium chloride solution
12. dry with materialdried over anhydrous sodium sulfate
13. distillationThe solvents were distilled off under a reduced pressure
14. customthe resulting residue was then purified by column chromatography (hexane-ethyl acetate=3:2)

ORD-Eintrag

ord-6c0c93c5a7694348b3b052e4c60c1873

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08377967B2